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Compare 375 Vacation Homes in Westport with updated reviews, rates, and availability.

Historic Connecticut Home w/ Grill & Spacious Yard

10.0 out of 10, Exceptional, (6)
"Very well appointed (Boll & Branch sheets so nice). Great communication from owners. "
Historic Connecticut Home w/ Grill & Spacious Yard

Captain's Cottage - Cold Spring Harbor Water Views

10.0 out of 10, Exceptional, (55)
"Great location, very comfortable, nicely decorated, and well stocked re necessities. "
The price is AED 727
AED 1,542 total
includes taxes & fees
30 Mar - 31 Mar
Captain's Cottage - Cold Spring Harbor Water Views

Lakeside luxury: beautiful, relaxing 4 bedroom home

10.0 out of 10, Exceptional, (19)
"This is a beautiful property. When we arrived, everything was perfect. It is completely stocked, including games for the family, and an unbelievable view of the lake. Communication with the homeowner was wonderful and we definitely plan to come back. We highly recommend this beautiful, clean and well kept home on the lake!."
Lakeside luxury: beautiful, relaxing 4 bedroom home

Business or Weekend escape

9.4 out of 10, Exceptional, (33)
"We had a wonderful stay here. It was the perfect man cave for a mom and two teenage boys! It was very clean and the host was amazing! He was very very helpful with questions we had and things that we needed in the area. I would definitely stay with him again."
The price is AED 275
AED 496 total
includes taxes & fees
30 Mar - 31 Mar
Business or Weekend escape

Cheerful 4 bedrooms residential house.

9.8 out of 10, Exceptional, (29)
"We had 8 people staying in the house. We were in town for a wedding. The house was well fitted for us. Kitchen had all the dishes we needed. Appliances all worked well. Nice walk to the sound. Neighborhood was kind of iffy but we had no problems. "
Cheerful 4 bedrooms residential house.

Bright Stylish Chic 4BR 4BA Home Pet Friendly!

10.0 out of 10, Exceptional, (96)
"House is absolutely perfect! This is our second time staying and we will definitely return. So much charm and warmth. I had the best sleep that I have had in months. All the amenities you could ask for, and more. Terrific convenient location. Host goes above and beyond to make sure we are comfortable. "
Bright Stylish Chic 4BR 4BA Home Pet Friendly!

Main Street Westport, walk to shops, dining, downtown

Main Street Westport, walk to shops, dining, downtown

BREATHTAKING BUNGALOW-HOME AWAY FROM HOME

10.0 out of 10, Exceptional, (27)
"We loved the location and the space was great for our visit. Very clean and cozy. Would recommend and we would book again if we are ever back in the area. "
BREATHTAKING BUNGALOW-HOME AWAY FROM HOME

Beach Front Arts & Crafts House With Gorgeous Views Of The Sound

10.0 out of 10, Exceptional, (116)
"The Arts and Crafts home was more beautiful than the pictures reflected! We loved all of the details in the woodwork, hidden little corners, tons of space to spread out and wonderful places to gather together. Having recently sold our "family home" we were thrilled to find this home in which to have a mini- family reunion. The kitchen was incredibly well-stocked- from serving platters to garlic powder to paper towels...We had everything we needed. The gas fireplace created a beautiful focal...
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound

Over Sized Colonial on Private Road.

9.6 out of 10, Exceptional, (39)
"The home was spacious and provided recreation for kids with hot tub, gym, ping pong, foosball, and game. However, property was advertised as 9 bedrooms and 7 baths. My family looked forward to spreading out but 4 bedrooms with adjoining bathrooms were locked. Text host to see if he would open them but he declined. That was disappointing."
Over Sized Colonial on Private Road.

New Beach Home near Stamford Downtown/Shippan

10.0 out of 10, Exceptional, (20)
"Great home with fun ping pong table!"
The price is AED 2,083
AED 3,815 total
includes taxes & fees
13 Apr - 14 Apr
New Beach Home near Stamford Downtown/Shippan

Ocean Front Beach House with Private Beach Access - Newly Renovated!

10.0 out of 10, Exceptional, (14)
"Communication was top notchThe property was very well appointed and perfect for a family gathering The most important part was the accessibility of the bathroom and bedroom for my mom who has mobility issues I was worried about the half step from bedroom to bathroom but I put pick lights on floor to remind her to step upLocation was perfect Especially loved visiting pez!"
Ocean Front Beach House with Private Beach Access - Newly Renovated!

Cottage at Sunny Day- Lakeside, views, kayak, dock

9.8 out of 10, Exceptional, (35)
"This property was very new and clean. It had everything you needed. Every room was comfortable and had its own TV. The open layout of the main floor made for great socializing and eating, and the 180 views of the frozen lake (in February) were beautifully serene. Would definitely come again and maybe next time in the summer! Thanks you for sharing this lovely property."
Cottage at Sunny Day- Lakeside, views, kayak, dock

Westport Gem - walk to shops, dining, town center, pet-friendly

10.0 out of 10, Exceptional, (3)
"After a rough year we were able to get a few days away and at the last minute chose this location. Everything we were looking for was there. The home and grounds were beautiful. The location in Westport was exactly what we wanted: magnificent fall foliage, quiet where the home was but close enough to walk to town and enjoy every aspect of being close by the town for lovely cafes and restaurants. Also, beautiful places were accessible by car in minutes such as Earthplace for trails and nature...
Westport Gem - walk to shops, dining, town center, pet-friendly

Spacious Gorgeous Getaway perfect for family reunion or business

9.8 out of 10, Exceptional, (6)
"The place was plenty big and had so many rooms so all of the atjletes on Team B*REAL had their own space. We loved the huge island in the kitchen and open space to hang out together."
Spacious Gorgeous Getaway perfect for family reunion or business

Spacious 4-bedroom house with WiFi and AC in awesome Milford

The price is AED 1,300
AED 2,619 total
includes taxes & fees
30 Mar - 31 Mar
Spacious 4-bedroom house with WiFi and AC in awesome Milford

Charming West Haven Home - Walk to Beach!

8.6 out of 10, Excellent, (11)
"Clean house in a convenient and quiet location. Close to many store and restaurants. House was well equipped. Sauna was a nice extra. Only complaints are that the bed in the third bedroom is not for adults and the towels need to be replaced. We would definitely rent the house again when in the area. "
Charming West Haven Home - Walk to Beach!

Breathtaking Waterfront house

9.4 out of 10, Exceptional, (3)
"The house was large, comfortable, and well appointed. The views looking out over the Bayville cove and Mill Neck were very pretty, and sitting out by the pool was enjoyable. We had a very nice and friendly greeter meet us when we arrived and she helped us choose from the many fine restaurants in the neighborhood. Overall we had a very pleasant stay."
Breathtaking Waterfront house

Cozy retreat with fenced in yard—centrally located in the heart of Long Island.

10.0 out of 10, Exceptional, (12)
"We had a wonderful stay at this property! The home was beautiful, well-maintained, and had everything we needed for a comfortable visit. The location was absolutely perfect—convenient to everything we needed to do in Huntington. The host was incredibly responsive and made sure we felt welcome from start to finish. We truly appreciated the attention to detail and would highly recommend this property to anyone looking for a great place to stay. We’d happily return in the future. "
Cozy retreat with fenced in yard—centrally located in the heart of Long Island.

Colonial steps from beach: 3BR, 2BA Oasis with Hot Tub

Colonial steps from beach: 3BR, 2BA Oasis with Hot Tub
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Westport

Main Street Westport, walk to shops, dining, downtown

Main Street Westport, walk to shops, dining, downtown

Westport Gem - walk to shops, dining, town center, pet-friendly

10.0 out of 10, Exceptional, (3)
"After a rough year we were able to get a few days away and at the last minute chose this location. Everything we were looking for was there. The home and grounds were beautiful. The location in Westport was exactly what we wanted: magnificent fall foliage, quiet where the home was but close enough to walk to town and enjoy every aspect of being close by the town for lovely cafes and restaurants. Also, beautiful places were accessible by car in minutes such as Earthplace for trails and nature...
Westport Gem - walk to shops, dining, town center, pet-friendly

DUNE Fairfield Beach

3.0 star property
8.8 out of 10, Excellent, (49)
"Really liked Dune. I had a great room that was on the other side from Sea Grape - bar that could be loud. I heard noting from room 31. Could walk to Post Rd and the beach. Ocean view from room. "
The price is AED 1,046
AED 1,574 total
includes taxes & fees
5 Apr - 6 Apr
DUNE Fairfield Beach
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.